


Figuring Things Out Is Hard

by NavajoLovesDestiel



Category: Supernatural
Genre: Alternate Universe, Dean Winchester Being an Idiot, Friends to Lovers, M/M, Marijuana, Punk Castiel/Nerd Dean Winchester, Roommates, Smut, Tattoos
Language: English
Status: Completed
Published: 2019-06-08
Updated: 2019-06-08
Packaged: 2020-04-23 00:40:18
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 4
Words: 4,253
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/19140115
Author URL: https://archiveofourown.org/users/NavajoLovesDestiel/pseuds/NavajoLovesDestiel
Summary: Cas was standing over the stove in his boxers, just like every other morning. But this morning, Dean took a moment to look at him. Really look.Dude had a nice ass. His legs were thick and muscular… runner’s thighs.Dean was caught up short. He was checking out Cas. His roommate Cas. His bro, Cas. His dick gave a twitch. He turned and hurried back to his bedroom.Dean felt a little panicky. His dick was half hard and the palmed it, willing it to go down. It listened about as well as it ever did, which is to say, it just got harder.He thought about Cas’ ass. That didn’t help his dick situation at all.When did he get turned on by Cas? How did he get turned on? What was going on?





	1. Chapter 1

**Author's Note:**

  * For [MaiMalfoi87](https://archiveofourown.org/users/MaiMalfoi87/gifts).



> This is a teeny thing I wrote for my spirit twin, maimalfoi87 birthday!  
> Happy birthday, kiddo! Love you like Dean loves pie.

No one got why Dean Winchester and Cas Novak were best friends. There couldn’t have been two more different men in the world. But best friends they were, and had been for over seven years, ever since they’d met freshman year of college.

Dean was just a regular guy. He worked restoring classic cars, loved cowboy movies and Star Wars. He drank beer and played pool.

Cas was a force of nature. He had tons of tattoos, wore eye makeup and had several piercings. He worked in IT, and preferred weed and staying home. He was more a Deadpool and Avengers kind of guy.

There was another difference between them. Dean dated women, Cas was openly gay.

And yet they were good friends. 

Did I mention they were also roommates? 

(OMG there was only one bed! No, wait, that’s a different story altogether…)

Dean had been dating a woman named Lisa off and on. He wasn’t serious about her, but he was beginning to think she was about him.

Cas occasionally brought home men, but never the same one twice. And they were never there in the morning. Lisa had stayed over a couple of times, but she and Cas didn’t really get along, so Dean tried to curb that.

Lisa actually hated Cas. “He’s weird.” “He’s not good for you to be around.” “He smokes too much weed.”

Dean just ignored her. Cas was his best friend, and he valued that more than he valued her opinion. That was kinda the problem. 

 

Dean came in from work on a Friday. Cas was sitting on the floor, his bong beside him.

“Long day?”

Dean kicked off his boots and put them by the front door. “Fuck yeah. Man, am I glad it’s Friday.”

Cas patted the floor next to him. ‘Cop a squat.” He held out the bong and a lighter.

“Hang on, let me get a beer.”

Two beers in hand, Dean went back and sat on the floor, leaning his back against the couch. He handed Cas a beer and took the bong.

He took a deep hit, holding the smoke in and leaned back again, letting the smoke roll out of his mouth.

Cas watched with a smile.

“I’m thinking of breaking up with Lisa.”

Cas tipped back the bottle and took a drink. “I don’t know what you see in her, Dean.”

Dean sat and thought. “Well, she has a banging body, and she does this thing with her tongue…”

Cas held up his hand. “Too much information. So, why you breaking up with her if she has such a talented tongue?”

Dean sighed. “I think she’s in love with me. Wants to be exclusive. I don’t feel that way about her.”

Cas nodded. “Just a good lay?”

Dean smiled. “Something like that, yeah.”

“You can do better, Dean.”

Dean took a long drink of his beer. “I dunno, Cas. I think I’m pretty much undateable.”

Cas laughed and took back the bong. “I never liked her.”

Dean grinned. “I know. She doesn’t like you either.”

Cas snorted. “All the more reason to break up with her.”

Dean grinned and took another hit. He sat back, thinking. He never could be with someone who didn’t like Cas. How he had ever put up with Lisa for so long, now escaped him.

They spent the evening getting high and drunk, laughing at everything.

Dean woke up the next morning to the sweet combination of scents that meant coffee and bacon. He sat up on the side of the bed and ran a hand through his hair.

No matter how hammered Cas got, he was always up early, always fixing food. Dean felt a surge of affection for his friend. A strong surge. 

Dean thought about it. He’d been having…  _ feelings _ … lately. Ones he didn’t really understand or feel comfortable with. Feelings about Cas.

He shook his head and got up. He did his thing in the bathroom and went out to greet that bacon.

Cas was standing over the stove in his boxers, just like every other morning. But this morning, Dean took a moment to look at him. Really look.

Dude had a nice ass. His legs were thick and muscular… runner’s thighs.

Dean was caught up short. He was checking out Cas. His roommate Cas. His  _ bro _ , Cas. His dick gave a twitch. He turned and hurried back to his bedroom.

Dean felt a little panicky. His dick was half hard and the palmed it, willing it to go down. It listened about as well as it ever did, which is to say, it just got harder.

He thought about Cas’ ass. That didn’t help his dick situation at all.

When did he get turned on by Cas? How did he get turned on? What was going on?

He wasn’t gay. He liked pussy. He was a pussy magnet. Sure, he’d kissed a couple of men in the past, but that didn’t mean anything, he’d been drunk.

And maybe he and Aaron had exchanged hand jobs when he was a junior in high school. That’s what horny teenagers did. It didn’t mean anything.

Or did it?

Dean jumped when there was a knock on his door.

“Dean, wakey, wakey. Breakfast is ready.”

Dean cleared his throat. “Okay, Cas, be out in a minute.”

He sounded weird, even to his own ears.

“Uh… okay. Dean, are you alright?”

Dean hurried to assure Cas he was just waking up, he was fine. He heard Cas’ steps leaving.

Dean knew he had to go out, eat his breakfast, talk to Cas. How could he go out there? What if he popped a woody out there?

He struggled to think of every non-sexy thing he could. By the time he got to his grandma’s panties, his dick was soft and he stood up. He took a deep breath and opened the door.

Cas was sitting at the table, and Dean could only see him from the waist up. He took a deep breath and sat down.

“Mornin’ sunshine.”

Cas looked up and smiled at him. “Good morning! You okay? I didn’t think you drank that much last night.”

Dean shook his head. “Not hungover, just didn’t sleep great. I’m fine.”

Cas went back to eating, so Dean ate. 

“So, what’s the plan today?” Cas chewed a piece of bacon and looked at Dean.

“Uh… no plans I think… I may go back to bed.”

Cas nodded. “You look like you need to.”

Dean got up and went to his room.

 


	2. Chapter 2

Dean managed to make it through the weekend, mostly by avoiding Cas.

He spent a lot of time on the internet, looking for information on bisexuality. He had never given much thought about it before, he wasn’t even sure it was a thing. Now, of course, he knew it was real, and more than that, he knew he was bi.

It was a hard thing to accept, but there it was, nevertheless. He not only had feelings for Cas, he had desires too.

If anyone could give him some advice, it was Charlie. He called her on Sunday and asked her to meet him at the bar. He didn’t need to say which one, it was understood he meant the Roadhouse.

 

They sat in a booth. Dean nervously picked the label off his beer bottle as he told Charlie what happened.

She smiled at him and patted his hand.

“I’m happy to hear you finally pulled your head out of your ass.”

Dean stared at her. “What? You mean, you…  _ knew _ ?”

Charlie laughed merrily. “Dean, everyone knew.”

Dean just gaped at her.

"What the fuck are you talking about, red?”

Charlie sighed. “Look, dumbass, you’ve been in love with Cas since college. I could see it, every one of your friends could see it. We just never thought you’d get there. Now you have. You need to go for it, Dean.”

Dean shook his head. “Cas is my best friend. Even if I have been… in love with him like you say, he’s my best friend. I’m not gonna do anything to mess that up. Besides, he isn’t in love with me.”

Charlie sighed. “Dean, Dean, Dean. For someone so smart, you really are mind-boggling stupid. Cas is in love with you. He always has been.”

Dean snorted. “You’re nuts. He isn’t in love with me! He never… he hasn’t… you’re nuts.”

Charlie snorted back at him. “He thinks you’re straight. What was he supposed to do?”

Dean’s head hurt. He got up, threw some money down on the table. He turned to Charlie and held up a finger. “Not a word about this to Cas!” He left.

 

Cas sat on the couch between Benny and Gabriel. He passed Benny the joint. Gabriel held out the bag of gummy worms. Cas shook his head no, and Gabriel shrugged and ate another one.

Benny passed the joint to Gabriel. 

“So what’s up, Cas? You look like someone ate your puppy.” Benny giggled at the statement.

Cas sighed. “Something’s up with Dean. He comes home from work, goes in his bedroom and hardly comes out. He isn’t talking to me. He’s… moping about something.”

Gabriel laughed. “Ah, your crush isn’t spending time with you? That’s tragic.”

Cas frowned at him. “Yeah, that’s it exactly. Jesus, Gabe. Give me a break.”

Benny chuckled. “Come on, Cas. you know Dean. Something crawled up his ass, but he’ll get over it and go back to paying attention to you.”

Cas sighed. “I hope so. This time it just feels… different.”

Benny put a hand on Cas’ shoulder. “He’ll come around. Don’t sweat it, Cas.” 

 

Gabriel looked at him. “I know how you feel about him, but come on. It’s been years. You need to find yourself someone who actually loves you back.”

Cas sighed again. “You’re probably right.”

 

Things continued like that for another week. Cas began to worry that Dean was going to move out. Finally on Friday night, he got stoned and knocked on Dean’s bedroom door.

Dean yelled, “Yeah?”

Cas opened the door a crack. “Dean, can we talk?”

Dean sighed. “Yeah, Cas, come on in.”

Dean took a deep breath. Cas came in and sat on the edge of the bed.

Dean waited, but Cas didn’t say anything.

“What’s up?”

Cas looked at him, and he looked so sad, Dean felt like a jerk.

“Dean, you need to tell me what I did. You’re obviously avoiding me. I don’t know what I did, but we need to talk about it.”

Dean felt even more like a jerk. “You didn’t do anything, Cas. It’s me. I’ve… I’ve been working through some stuff.”

Cas sighed. “Dean, tell me. Maybe I can help. Maybe I can’t, but this is killing me.” He waved a hand between the two of them.

Dean looked away. “I can’t Cas. I… it’s just something I have to work out for myself.”

Cas looked close to tears. “Dean, please don’t move out!”

Dean looked back at him. “Move out? Why would I move out?”

Cas shook his head. ‘We haven’t talked in weeks. You just stay in your room or go out and stay gone until late. What am I supposed to think?”

Now Dean felt even worse. He didn’t mean to forget about Cas and make him feel like Dean was mad at him. He was just mad at himself. 

“Cas, look. You haven’t done a thing. I’ve just been trying to work some stuff out. I’m sorry I ignored you. Come on, let’s smoke a J and talk.”

Dean got up and so did Cas. They walked to the living room and sat on the floor. Cas grabbed his bong and loaded it. He handed it to Dean with the lighter.

An hour later, Dean couldn’t even remember what the problem was. So what if he was bi? Lots of people were, if the internet was any indication. He sat back and listened to Bad Wolf sing Zombie.

Cas was singing along. Dean looked at him with a smile. Cas was the most gorgeous man Dean had ever seen. He’d always thought so. 

Dean started to sing too. Cas grinned at him. Dean stared at Cas. Cas stared back.

Before he had time to think about or even knew what he was doing, he leaned over and kissed Cas.

Cas stiffened and pulled away. “Dean, what are you doing?”

Dean blushed. “I thought I was kissing you.”

Cas stared at him like he’d lost his mind. “Dean, you’re straight. You don’t kiss guys.”

Dean rubbed the back of his neck. “Yeah, well, about that. I… I might not be exactly straight.”

Cas really stared at him now. “What the everloving fuck are you talking about?”

Dean chuckled. “That’s what I’ve been thinking about so hard. I guess I have…  _ feelings _ for you.”

Cas just sat there, staring. Dean rubbed the back of his neck again, beginning to feel wildly uncomfortable. His happy high was gone.

Finally, Cas leaned forward and kissed Dean. This time, Dean was stiff, but he got into it quickly. 

Dean had no idea how long they’d been kissing. The only things in his mind were how soft Cas’ lips were, soft and full, and what a great kisser Cas was. This was by far the best kissing he’d ever been a part of.

Cas pulled away. Dean absolutely did not whine.

“Dean, talk to me. What changed?”

Dean chuckled. “I looked at your ass.”

Cas tilted his head. “You... looked at my  _ ass _ ?”

Dean smiled. “Yep. You were fixing breakfast in those bumblebee boxers. I looked at your ass and it gave me a chubby.”

Cas shook his head. “So, you got hard, seeing me in my boxers, when you’ve probably seen me in my boxers a thousand times before?”

Dean nodded. “I can’t explain it. But it really turned me on.”

 


	3. Chapter 3

Dean was laid out under Cas, naked and afraid. He wondered if he would be able to do this. Even though he was hard as granite, leaking precome onto his balls, he was scared out of his head. 

Cas sensed how he was feeling and kissed him, over and over. Dean relaxed.

Cas pulled back. “Dean, nothing is going to happen that you don’t want to happen. Just relax, please.”

Dean looked up into the ocean that was Cas’ eyes. “Cas, I want this, I do. I just don’t know what to expect. I have no idea what I’m doing here.’

Cas smiled. Dean thought about how that smile lit up his world and smiled back.

“Dean, do you trust me?”

“With my life, Cas.”

Cas nodded. “Just relax and let me take care of you. I’d never hurt you, I swear.”

Dean sighed. “I know that, Cas. I’m okay.”

Cas kissed him again, running his tongue along Dean’s. Dean sucked on it.

Then Cas kissed along his jaw, behind his ear, down his throat. Dean turned his head, and just let the anxiety go. Cas was going to take care of him.

Cas licked around Dean’s nipple and then sucked on it. Dean heard himself moan. Cas did the same to the other nipple and then kissed and licked down lower.

The closer Cas’ mouth got to his cock, the more Dean wanted it. When Cas kissed the head of his dick, he groaned.

“Cas… “

Cas shushed him and sucked Dean’s cock into his mouth. Dean felt like his brain was going to explode. It was so good, so wet and warm… not at all like a woman’s mouth. Cas wanted Dean’s dick in his mouth and knew what to do with it. 

It was the best blow job Dean had ever gotten. Cas was skillful with his tongue, could take all of Dean’s dick into his throat without gagging… it was amazing. Dean could feel his balls tighten far too soon.

Cas didn’t pull off. He took every drop that came out of Dean and swallowed it all. Cas let Dean’s floppy dick fall from his mouth and Dean pulled him up into a kiss. It was the first time in his life he’d tasted himself.

Cas laid down next to him. Dean caught his breath.

“That was… awesome, Cas. The best blow job ever.”

Cas chuckled. “Well, I do know my way around a dick.”

Dean laughed. “Yeah, you do.”

Dean laid back or a moment.

“Okay, Cas, I’m going to reciprocate.”

Cas put a hand on Dean’s arm. “Dean you don’t have to.”

Dean smiled at him. “I want to, Cas. I’ve never… you know, before, so I might suck at it.”

Cas laughed. “Sucking is kind of the whole point.”

Dean grinned. “Ha ha asshole.”

He moved down and looked at Cas’ cock for the first time. It was thick, thicker than his, and about as long. Cas was hard, a pearl drop of precum glistened at the tip.

Dean took a tentative lick. It was a little bitter, a little salty, but not that bad. Cas gasped.

Dean took the head in his mouth. He paused, just experiencing the feeling. It was… interesting. Not bad. Not bad at all. He sucked down a little, just feeling the heft and the stretch. He liked the feeling. He sucked down further.

He grabbed the shaft in his hand. He knew if he tried to suck all the way down, he’d just end up gagging, possibly throwing up. And that was about as far from sexy as a person could get.

So he went back up, then back down again as far as he dared, and used his hand on the rest. Cas was moaning, and Dean loved that sound.  _ He _ was the reason…  _ he _ was making Cas moan. 

He loved it. He could get used to this.

He kept it up, using his hand in rhythm with his mouth. He played with Cas’ balls with his other hand.

Cas grabbed a handful of his hair. “Dean… I’m close…”

Dean knew he wasn’t ready for a mouth full of cum, so he pulled his mouth off and just used his hand. It didn’t take more than a few tugs and Cas was coming. Cum covered his hand and hit Cas in the belly.

He laid back, listening to Cas pant. When he caught his breath, Cas got up and got a washcloth and cleaned them both off.

When they were laying wrapped around each other, Cas looked at him.

“Is this real, Dean? I’ve wanted this for so long, I’m having a little trouble wrapping my mind around it.”

Dean sighed. “Yeah, it’s real. I’m sorry, Cas, sorry it took me so long to get my head out of my ass and realize how I felt about you.”

Cas laughed. “As long as you finally have, I’m satisfied.”

He lifted his head to look at Dean. “You have, right? This isn’t just a one time thing. You aren’t going back to Lisa, are you?”

Dean laughed. “No, I’m not going back. All I want is you, Cas.”

Cas kissed him.

They slept. When they woke up, Cas took them both in hand and jacked them off. Dean couldn’t believe how amazing it was, feeling Cas’ cock rubbing against his. He came so hard, he saw stars.

Cas drifted off to sleep, but Dean laid there, thinking. He was wrapped in Cas’ arms and it felt so right, he felt like he could cry. Why had he been so thick-headed all those years? He could have had this. Sighing, he chalked that up to water under the bridge. Cas murmured in his sleep and Dean smiled.

“You’re thinking too hard, Dean. Go to sleep.”

Dean kissed Cas’ forehead. “Not sleepy.”

Cas lifted his head and looked at him. “Horny?”

Dean laughed. “Maybe…”

Cas grinned. “I never knew you were so insatiable.”

“Never was before you.”

The look on Cas’ face was worth a million dollars.

Cas kissed him and it got hot and messy in no time. 

When Cas went to move down, Dean grabbed him.

“I want you, Cas. I want you… inside me.”

Cas was shocked. “Dean, are you sure? I mean, you’re a virgin when it comes to this.”

Dean laughed. “And I always will be, unless you fuck me. Come on, Cas, you know you want to.” He wiggled his hips.

Cas growled deep in his throat and leaned over to grab a condom and the lube. Dean spread his legs and Cas settled between them.

 

 


	4. Chapter 4

Cas took his time. Dean was a mess, sweaty, moaning, begging for Cas to get on with it.

“It’s your first time, Dean. I need to know I won’t hurt you. Be patient.”

Dean mumbled under his breath, “Fuck patience.” But he knew arguing with Cas would get him exactly nowhere.

Cas worked Dean open, scissoring his fingers, then adding another one. He kept it up until he had four fingers in Dean, and neither he or Dean could wait anymore.

He pulled his fingers out and heard Dean whimper. He hurried to roll the condom on then lined up. He pressed the head of his dick to Dean’s hole and pushed.

Dean gasped when the head of Cas’ cock entered him. It was the weirdest feeling he’d ever had. It stretched him and it burned, but the burn lessened as Cas held there. Dean nodded.

Cas pushed in more, then held again. Dean felt so full, he couldn’t believe Cas wasn’t in all the way yet. But then Cas pushed in more, and Dean felt Cas’ balls on his ass.

 

Cas didn’t move, as much as he wanted to. He looked down at Dean, looking for any signs of pain or panic. He didn’t see anything, just Dean with his eyes big. He leaned over and kissed Dean, pulling back slowly. Dean felt impossibly tight. Cas pulled his mouth away to moan. As he pushed back in just as slowly, Dean groaned.

Cas stopped, not knowing if that was a groan of pain or not. 

“Cas, move, or swear to fuck I’ll hit you.”

Cas laughed and pushed back in. he pulled back again and found a rhythm.

Dean grabbed his arms. “Oh shit, it feels so good, Cas… I... “ 

It just became a moan.

Cas still could hardly believe this was real. He’d loved Dean for so many years, and he’d given up on any idea that this would ever happen. He’d noticed Dean checking guys out more than once, but Dean always steadfastly maintained that he was straight. 

Now, here he was, under Cas, Cas inside him… it was nothing short of a miracle.

 

Dean couldn’t believe how good it felt. Every once in a while, Cas’ dick would rub against his prostate and it lit him up from the inside out like being electrocuted. He dug his fingers into Cas’ arm, just looking for something to hang on to, to keep from slipping off the edge of the world.

He was so close. He just needed a little help to get there. He tightened his legs around Cas’ hips and grabbed his cock. He ran his hand up and down his cock, maybe three times before he felt his balls tighten and he just managed to gasp out that he was going to cum when he did. He came so hard he was fairly sure he blacked out for a moment.

He could hear himself yell, but it sounded far away.

 

Cas heard Dean gasp and say something he couldn’t make out, and then Dean came. His hole tightened on Cas’ cock and then relaxed. When it tightened again, that was it. Cas came. He heard Dean yell, but he had to squeeze his eyes shut with the intensity of his orgasm.

When it was over, Cas thrust in and out a few times, letting his dick get soft. Then he pulled out and sat back, looking at his cum leak out of Dean.

He took off the condom and threw it somewhere. He collapsed on the bed next to Dean and caught his breath.

 

They laid facing each other, their legs tangled together and embraced. They kissed, slowly, sweetly, as if they had all the time in the world.

Dean pulled back. “Cas, I can’t believe I wasted the last seven years, when we could have been together, doing  _ this _ . I’m so sorry I was such an idiot.”

Cas smiled at him. “I forgive you, dumbass. At least you finally figured it out. I could have told you how I felt about you. But I was scared you’d run away, never talk to me again.”

Dean nodded. “I probably would have told you that you were nuts.”

Cas kissed Dean’s forehead.

Dean looked at him, his eyes wet. “Cas, you’re it for me, I need you to know that. You’re my home. You always have been. I just couldn’t admit it to myself. But now? You’re all I want.”

Cas sighed. “Dean, I love you. I have ever since I first saw your nerdy ass, wandering around the library. You’re all I ever wanted.”

Dean blushed. “Well, I do have an awesome ass.”

Cas laughed. “That you do.”

Dean took a deep breath. “I love you too, Cas. I always have. I knew I loved you, I just didn’t know I was  _ in _ love with you.”

Cas smiled. “Well, we have all the time in the world, now, to make up for the past seven years.”

 


End file.
